Transition-Metal-Free
Synthesis of C‑Glycosylated
Phenanthridines via K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>‑Mediated
Oxidative Radical Decarboxylation of Uronic Acids
Xin Zhou
Peng Wang
Li Zhang
Pengwei Chen
Mingxu Ma
Ni Song
Sumei Ren
Ming Li
10.1021/acs.joc.7b02346.s002
https://acs.figshare.com/articles/dataset/Transition-Metal-Free_Synthesis_of_C_Glycosylated_Phenanthridines_via_K_sub_2_sub_S_sub_2_sub_O_sub_8_sub_Mediated_Oxidative_Radical_Decarboxylation_of_Uronic_Acids/5747184
We
have developed an efficient protocol for the synthesis of C-glycosylated
phenanthridines. Tetrafuranos-4-yl and pentapyranos-5-yl radicals,
generated from K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>-mediated oxidative
decarboxylation of furan- and pyranuronic acids, undergo attack to
2-isocyanodiphenyls and ensuing homolytic aromatic substitution to
provide diverse C-glycosylated phenanthridines in satisfactory yields
without resort to transition metals. This reaction tolerates various
functional groups, and enables ready synthesis of complex oligosaccharide-based
phenanthridines. The C-glycosylated phenanthridine derived from β-cyclodextrin
has been prepared, which might be potential in medicinal and biological
chemistry due to its flexible conformation.
2017-12-20 00:00:00
C-glycosylated phenanthridines
synthesis
pentapyranos -5-yl radicals
K 2 S 2 O 8